Ether containing siloxy compounds

ABSTRACT

The present invention relates to compounds of the formulawhere R1, R2 and R3 are independently selected from alkoxy radicals having from 1 to 8 carbon atoms; R4 and R5 are independently selected from the group consisting of alkylene having 1 to 12 carbons, arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbon atoms and n is an integer of from 1 to 10. These compounds may be used in rubber compositions.

This Appln claims benefit of Prov. No. 60/148,174 filed Aug. 10, 1999.

FIELD OF THE INVENTION

The present invention relates to ether containing siloxy compounds whichmay be used as silica couplers in rubber. The present invention alsorelates to a silica-filled rubber composition containing ethercontaining siloxy compounds and the processing of a sulfur-curablerubber composition containing silica and ether containing siloxycompounds.

BACKGROUND OF THE INVENTION

Sulfur containing organosilicon compounds are useful as reactivecoupling agents between rubber and silica fillers providing for improvedphysical properties. They are also useful as adhesion primers for glass,metals and other substrates.

U.S. Pat. Nos. 3,842,111, 3,873,489 and 3,978,103 disclose thepreparation of various sulfur containing organosilicon compounds. Theseorganosilicon compounds are prepared by reacting

(a) 2 moles of a compound of the formula:

Z—Alk—hal

where hal is a chlorine, bromine or iodine; Z is:

where R¹ is an alkyl of 1 to 4 carbon atoms or phenyl and R² is alkoxyof 1 to 8 carbon atoms; or cycloalkoxy of 5 to 8 carbon atoms; oralkylmercapto with 1 to 8 carbon atoms; Alk is a divalent aliphatichydrocarbon or unsaturated hydrocarbon or a cyclic hydrocarboncontaining 1 to 18 carbon atoms; with

(b) 1 mole of a compound of the formula:

Me₂S_(n)

where Me is ammonium or a metal atom and n is a whole number from 2 to6.

SUMMARY OF THE INVENTION

The present invention relates to ether containing siloxy compounds andtheir use in silica-filled rubber.

DETAILED DESCRIPTION OF THE INVENTION

There is disclosed a compound of the formula:

where R¹, R² and R³ are independently selected from alkoxy radicalshaving from 1 to 8 carbon atoms; R⁴ and R⁵ are independently selectedfrom the group consisting of alkylenes having 1 to 12 carbon atoms,arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbonatoms and n is an integer of from 1 to 10.

There is also disclosed a method for processing a rubber compositionwhich comprises mixing

(i) 100 parts by weight of at least one sulfur vulcanizable elastomerselected from conjugated diene homopolymers and copolymers and fromcopolymers of at least one conjugated diene and aromatic vinyl compound;with

(ii) 0.05 to 10 phr of a compound of the formula:

where R¹, R² and R³ are independently selected from alkoxy radicalshaving from 1 to 8 carbon atoms; R⁴ and R⁵ are independently selectedfrom the group consisting of alkylenes having 1 to 12 carbon atoms,arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbonatoms and n is an integer of from 1 to 10.

There is also disclosed a sulfur-vulcanizable rubber compositioncomprising an elastomer containing olefinic unsaturation and a compoundof the formula:

where R¹, R² and R³ are independently selected from alkoxy radicalshaving from 1 to 8 carbon atoms; R⁴ and R⁵ are independently selectedfrom the group consisting of alkylenes having 1 to 12 carbon atoms,arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbonatoms and n is an integer of from 1 to 10.

The present invention may be used to process sulfur vulcanizable rubbersor elastomers containing olefinic unsaturation. The phrase “rubber orelastomer containing olefinic unsaturation” is intended to include bothnatural rubber and its various raw and reclaim forms as well as varioussynthetic rubbers. In the description of this invention, the terms“rubber” and “elastomer” may be used interchangeably, unless otherwiseprescribed. The terms “rubber composition,” “compounded rubber” and“rubber compound” are used interchangeably to refer to rubber which hasbeen blended or mixed with various ingredients and materials and suchterms are well known to those having skill in the rubber mixing orrubber compounding art. Representative synthetic polymers are thehomopolymerization products of butadiene and its homologues andderivatives, for example, methylbutadiene, dimethylbutadiene andpentadiene as well as copolymers such as those formed from butadiene orits homologues or derivatives with other unsaturated monomers. Among thelatter are acetylenes, for example, vinyl acetylene; olefins, forexample, isobutylene, which copolymerizes with isoprene to form butylrubber; vinyl compounds, for example, acrylic acid, acrylonitrile (whichpolymerize with butadiene to form NBR), methacrylic acid and styrene,the latter compound polymerizing with butadiene to form SBR, as well asvinyl esters and various unsaturated aldehydes, ketones and ethers,e.g., acrolein, methyl isopropenyl ketone and vinylethyl ether. Specificexamples of synthetic rubbers include neoprene (polychloroprene),polybutadiene (including cis-1,4-polybutadiene), polyisoprene (includingcis-1,4-polyisoprene), butyl rubber, halobutyl rubber such aschlorobutyl rubber or bromobutyl rubber, styrene/isoprene/butadienerubber, copolymers of 1,3-butadiene or isoprene with monomers such asstyrene, acrylonitrile and methyl methacrylate, as well asethylene/propylene terpolymers, also known as ethylene/propylene/dienemonomer (EPDM), and in particular, ethylene/propylene/dicyclopentadieneterpolymers. Additional examples of rubbers which may be used includesilicon-coupled and tin-coupled star-branched polymers. The preferredrubber or elastomers are polybutadiene and SBR.

In yet another aspect of the present invention, it is preferred to use arubber or elastomer containing olefinic unsaturation and an additionalfunctional group reactive with the siloxy compounds of Formula I of thepresent invention. Representative functional groups include halogens,such as Cl and Br; alkoxy groups, such as methoxy groups; and,pseudohalogens, such as —SCN.

In yet another aspect of the invention, the elastomer may be asiloxy-terminated styrene-butadiene copolymer, siloxy-terminatedisoprene-butadiene copolymer and siloxy-terminatedstyrene-isoprene-butadiene terpolymer.

In one aspect the rubber is preferably of at least two of diene basedrubbers. For example, a combination of two or more rubbers is preferredsuch as cis 1,4-polyisoprene rubber (natural or synthetic, althoughnatural is preferred), 3,4-polyisoprene rubber,styrene/isoprene/butadiene rubber, emulsion and solution polymerizationderived styrene/butadiene rubbers, cis 1,4-polybutadiene rubbers andemulsion polymerization prepared butadiene/acrylonitrile copolymers.

In one aspect of this invention, an emulsion polymerization derivedstyrene/butadiene (E-SBR) might be used having a relatively conventionalstyrene content of about 20 to about 28 percent bound styrene or, forsome applications, an E-SBR having a medium to relatively high boundstyrene content, namely, a bound styrene content of about 30 to about 45percent.

The relatively high styrene content of about 30 to about 45 for theE-SBR can be considered beneficial for a purpose of enhancing traction,or skid resistance, of the tire tread. The presence of the E-SBR itselfis considered beneficial for a purpose of enhancing processability ofthe uncured elastomer composition mixture, especially in comparison to autilization of a solution polymerization prepared SBR (S-SBR).

By emulsion polymerization prepared E-SBR, it is meant that styrene and1,3-butadiene are copolymerized as an aqueous emulsion. Such are wellknown to those skilled in such art. The bound styrene content can vary,for example, from about 5 to about 50 percent. In one aspect, the E-SBRmay also contain acrylonitrile to form a terpolymer rubber, as E-SBAR,in amounts, for example, of about 2 to about 30 weight percent boundacrylonitrile in the terpolymer.

Emulsion polymerization prepared styrene/butadiene/acrylonitrilecopolymer rubbers containing about 2 to about 40 weight percent boundacrylonitrile in the copolymer are also contemplated as diene basedrubbers for use in this invention.

The solution polymerization prepared SBR (S-SBR) typically has a boundstyrene content in a range of about 5 to about 50, preferably about 9 toabout 36, percent. The S-SBR can be conveniently prepared, for example,by organo lithium catalyzation in the presence of an organic hydrocarbonsolvent.

A purpose of using S-SBR is for improved tire rolling resistance as aresult of lower hysteresis when it is used in a tire tread composition.

The 3,4-polyisoprene rubber (3,4-PI) is considered beneficial for apurpose of enhancing the tire's traction when it is used in a tire treadcomposition. The 3,4-PI and use thereof is more fully described in U.S.Pat. No. 5,087,668 which is incorporated herein by reference. The Tgrefers to the glass transition temperature which can conveniently bedetermined by a differential scanning calorimeter at a heating rate of10° C. per minute.

The cis 1,4-polybutadiene rubber (BR) is considered to be beneficial fora purpose of enhancing the tire tread's wear, or treadwear. Such BR canbe prepared, for example, by organic solution polymerization of1,3-butadiene. The BR may be conveniently characterized, for example, byhaving at least a 90 percent cis 1,4-content.

The cis 1,4-polyisoprene and cis 1,4-polyisoprene natural rubber arewell known to those having skill in the rubber art.

The term “phr” as used herein, and according to conventional practice,refers to “parts by weight of a respective material per 100 parts byweight of rubber, or elastomer.”

The ether containing siloxy compounds used in the present invention areof the formula:

where R¹, R² and R³ are independently selected from alkoxy radicalshaving from 1 to 8 carbon atoms; R⁴ and R⁵ are independently selectedfrom the group consisting of alkylenes having 1 to 12 carbon atoms,arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbonatoms and n is an integer of from 1 to 10. Preferably, each R¹, R² andR³ are alkoxy radicals having from 1 to 3 carbon atoms; R⁴ and R⁵ areeach an alkylene having from 1 to 5 carbon atoms and n is 1. The ethercontaining siloxy compounds of Formula I may comprise a high purityproduct or mixture of products of Formula I.

The compound of Formula I is added to the rubber in an amount rangingfrom 0.05 to 10 phr. Preferably, the amount ranges from 1 to 5 phr.

Representative of the ether containing compounds of Formula I includebut are not limited to:

wherein x and y are individually selected from a group of integers offrom 1 to 12 and R⁶ is a cycloaliphatic group having from 5 to 8 carbonatoms in the ring. Preferably, x is from 1 to 5, y is from 1 to 5 and R⁶is a cycloaliphatic group having 5 carbon atoms in the ring.

The siloxy compound of Formula I may be prepared by the reaction schemelisted below:

2SiCl₄+Cl—R⁴—O—R⁵Cl+4Na→Cl₃Si—R⁴—O—R⁵—Si—Cl₃+4NaCl

The reaction may be conducted in the presence of a suitable solvent. Theprimary criteria is to use a solvent which does not react with thestarting materials or end product. Representative organic solventsinclude hexane, heptane, cyclohexane, xylene, benzene and toluene. Wateris avoided to prevent reaction with the sodium and the siloxy groups ofthe compounds.

For ease in handling, the siloxy of Formula I may be used per se or maybe deposited on suitable carriers. Examples of carriers which may beused in the present invention include silica, carbon black,alumina-silicates, alumina, clay, kieselguhr, cellulose, silica gel andcalcium silicate.

The rubber composition should contain a sufficient amount of filler, ifused, to contribute a reasonably high modulus and high resistance totear. The filler may be added in amounts ranging from 10 to 150 phr.Representative fillers include silica, carbon black, aluminasilicates,clays, zeolites, modified starches, silica/carbon composites and thelike. Preferably, silica is present in an amount ranging from 10 to 80phr. If carbon black is also present, the amount of carbon black, ifused, may vary. Generally speaking, the amount of carbon black will varyfrom 0 to 80 phr. Preferably, the amount of carbon black will range from0 to 40 phr. It is to be appreciated that the silica coupler may be usedin conjunction with a carbon black, namely pre-mixed with a carbon blackprior to addition to the rubber composition, and such carbon black is tobe included in the aforesaid amount of carbon black for the rubbercomposition formulation.

Where the rubber composition contains both silica and carbon black, theweight ratio of silica to carbon black may vary. For example, the weightratio may be as low as 1:5 to a silica to carbon black weight ratio of30:1. Preferably, the weight ratio of silica to carbon black ranges from1:3 to 5:1. The combined weight of the silica and carbon black, asherein referenced, may be as low as about 30 phr, but is preferably fromabout 45 to about 90 phr.

The commonly employed siliceous pigments used in rubber compoundingapplications can be used as the silica in this invention, includingpyrogenic and precipitated siliceous pigments (silica), althoughprecipitate silicas are preferred. The siliceous pigments preferablyemployed in this invention are precipitated silicas such as, forexample, those obtained by the acidification of a soluble silicate,e.g., sodium silicate.

Such silicas might be characterized, for example, by having a BETsurface area, as measured using nitrogen gas, preferably in the range ofabout 40 to about 600, and more usually in a range of about 50 to about300 square meters per gram. The BET method of measuring surface area isdescribed in the Journal of the American Chemical Society, Volume 60,page 304 (1930).

The silica may also be typically characterized by having adibutylphthalate (DBP) absorption value in a range of about 100 to about400, and more usually about 150 to about 300.

The silica might be expected to have an average ultimate particle size,for example, in the range of 0.01 to 0.05 micron as determined by theelectron microscope, although the silica particles may be even smaller,or possibly larger, in size.

Various commercially available silicas may be considered for use in thisinvention such as, only for example herein, and without limitation,silicas commercially available from PPG Industries under the Hi-Siltrademark with designations 210, 243, etc; silicas available fromRhone-Poulenc, with, for example, designations of Z1165MP and Z165GR andsilicas available from Degussa AG with, for example, designations VN2and VN3, etc.

The siloxy compounds of Formula I may be used alone and/or incombination with a symmetrical sulfur containing organosilicon compound.Examples of suitable sulfur containing organosilicon compounds are ofthe formula:

Z—Alk—S_(n)—Alk—Z  (II)

in which Z is selected from the group consisting of:

where R⁷ is an alkyl group of 1 to 4 carbon atoms, cyclohexyl or phenyl;

R⁸ is alkoxy of 1 to 8 carbon atoms, or cycloalkoxy of 5 to 8 carbonatoms;

Alk is a divalent hydrocarbon of 1 to 18 carbon atoms and n is aninteger of 2 to 8.

Specific examples of sulfur containing organosilicon compounds which maybe used in accordance with the present invention include:3,3′-bis(triethoxysilylpropyl) disulfide, 3,3′-bis(triethoxysilylpropyl)tetrasulfide, 3,3′-bis(triethoxysilylpropyl) octasulfide,3,3′-bis(trimethoxysilylpropyl) tetrasulfide,2,2′-bis(triethoxysilylethyl) tetrasulfide,3,3′-bis(trimethoxysilylpropyl) trisulfide,3,3′-bis(triethoxysilylpropyl) trisulfide,3,3′-bis(tributoxysilylpropyl) disulfide,3,3′-bis(trimethoxysilylpropyl) hexasulfide,3,3′-bis(trimethoxysilylpropyl) octasulfide,3,3′-bis(trioctoxysilylpropyl) tetrasulfide,3,3′-bis(trihexoxysilylpropyl) disulfide,3,3′-bis(tri-2″-ethylhexoxysilylpropyl) trisulfide,3,3′-bis(triisooctoxysilylpropyl) tetrasulfide,3,3′-bis(tri-t-butoxysilylpropyl) disulfide, 2,2′-bis(methoxy diethoxysilyl ethyl) tetrasulfide, 2,2′-bis(tripropoxysilylethyl) pentasulfide,3,3′-bis(tricyclonexoxysilylpropyl) tetrasulfide,3,3′-bis(tricyclopentoxysilylpropyl) trisulfide,2,2′-bis(tri-2″-methylcyclohexoxysilylethyl) tetrasulfide,-bis(trimethoxysilylmethyl) tetrasulfide, 3-methoxy ethoxy propoxysilyl3′-diethoxybutoxysilylpropyltetrasulfide, 2,2′-bis(dimethylmethoxysilylethyl) disulfide, 2,2′-bis(dimethyl sec.butoxysilylethyl)trisulfide, 3,3′-bis(methyl -butylethoxysilylpropyl) tetrasulfide,3,3′-bis(di t-butylmethoxysilylpropyl) tetrasulfide, 2,2′-bis(phenylmethyl methoxysilylethyl) trisulfide, 3,3,′-bis(diphenylisopropoxysilylpropyl) tetrasulfide, 3,3′-bis(diphenylcyclohexoxysilylpropyl) disulfide, 3,3′-bis(dimethylethylmercaptosilylpropyl) tetrasulfide, 2,2′-bis(methyldimethoxysilylethyl) trisulfide, 2,2′-bis(methylethoxypropoxysilylethyl) tetrasulfide, 3,3′-bis(diethylmethoxysilylpropyl) tetrasulfide, 3,3′-bis(ethyldi-sec.butoxysilylpropyl) disulfide, 3,3′-bis(propyldiethoxysilylpropyl) disulfide, 3,3′-bis(butyl dimethoxysilylpropyl)trisulfide, 3,3′-bis(phenyl dimethoxysilylpropyl) tetrasulfide, 3-phenylethoxybutoxysilyl 3′-trimethoxysilylpropyl tetrasulfide,4,4′-bis(trimethoxysilylbutyl) tetrasulfide,6,6′-bis(triethoxysilylhexyl) tetrasulfide,12,12′-bis(triisopropoxysilyl dodecyl) disulfide,18,18′-bis(trimethoxysilyloctadecyl) tetrasulfide,18,18′-bis(tripropoxysilyloctadecenyl) tetrasulfide,4,4′-bis(trimethoxysilyl-buten-2-yl) tetrasulfide,4,4′-bis(trimethoxysilylcyclohexylene) tetrasulfide,5,5′-bis(dimethoxymethylsilylpentyl) trisulfide,3,3′-bis(trimethoxysilyl-2-methylpropyl) tetrasulfide,3,3′-bis(dimethoxyphenylsilyl-2-methylpropyl) disulfide.

The preferred sulfur containing organosilicon compounds are the3,3′-bis(trimethoxy or triethoxy silylpropyl) sulfides. The mostpreferred compounds are 3,3′-bis(triethoxysilylpropyl) tetrasulfide and3,3′-bis(triethoxysilylpropyl) disulfide. Therefore, as to Formula II,preferably Z is:

where R⁸ is an alkoxy of 2 to 4 carbon atoms, with 2 carbon atoms beingparticularly preferred; Alk is a divalent hydrocarbon of 2 to 4 carbonatoms with 3 carbon atoms being particularly preferred; and n is aninteger of from 3 to 5 with 4 being particularly preferred.

The amount of the sulfur containing organosilicon compound of Formula IIin a rubber composition will vary depending on the level of silica thatis used. Generally speaking, the amount of the compound of Formula IIwill range from 0 to 1.0 parts by weight per part by weight of thesilica. Preferably, the amount will range from 0 to 0.4 parts by weightper part by weight of the silica.

It is readily understood by those having skill in the art that therubber composition would be compounded by methods generally known in therubber compounding art, such as mixing the various sulfur-vulcanizableconstituent rubbers with various commonly used additive materials suchas, for example, sulfur donors, curing aids, such as activators andretarders and processing additives, such as oils, resins includingtackifying resins and plasticizers, fillers, pigments, fatty acid, zincoxide, waxes, antioxidants and antiozonants and peptizing agents. Asknown to those skilled in the art, depending on the intended use of thesulfur vulcanizable and sulfur vulcanized material (rubbers), theadditives mentioned above are selected and commonly used in conventionalamounts. Typical amounts of reinforcing type carbon blacks(s), for thisinvention, if used, are herein set forth. Representative examples ofsulfur donors include elemental sulfur (free sulfur), an aminedisulfide, polymeric polysulfide and sulfur olefin adducts. Preferably,the sulfur vulcanizing agent is elemental sulfur. The sulfur vulcanizingagent may be used in an amount ranging from 0.5 to 8 phr, with a rangeof from 1.5 to 6 phr being preferred. Typical amounts of tackifierresins, if used, comprise about 0.5 to about 10 phr, usually about 1 toabout 5 phr. Typical amounts of processing aids comprise about 1 toabout 50 phr. Such processing aids can include, for example, aromatic,napthenic, and/or paraffinic processing oils. Typical amounts ofantioxidants comprise about 1 to about 5 phr. Representativeantioxidants may be, for example, diphenyl-p-phenylenediamine andothers, such as, for example, those disclosed in the Vanderbilt RubberHandbook (1978), pages 344-346. Typical amounts of antiozonants compriseabout 1 to 5 phr. Typical amounts of fatty acids, if used, which caninclude stearic acid comprise about 0.5 to about 3 phr. Typical amountsof zinc oxide comprise about 2 to about 5 phr. Typical amounts of waxescomprise about 1 to about 5 phr. Often microcrystalline waxes are used.Typical amounts of peptizers comprise about 0.1 to about 1 phr. Typicalpeptizers may be, for example, pentachlorothiophenol anddibenzamidodiphenyl disulfide.

In one aspect of the present invention, the sulfur vulcanizable rubbercomposition is then sulfur-cured or vulcanized.

Accelerators are used to control the time and/or temperature requiredfor vulcanization and to improve the properties of the vulcanizate. Inone embodiment, a single accelerator system may be used, i.e., primaryaccelerator. The primary accelerator(s) may be used in total amountsranging from about 0.5 to about 4, preferably about 0.8 to about 1.5,phr. In another embodiment, combinations of a primary and a secondaryaccelerator might be used with the secondary accelerator being used insmaller amounts, such as from about 0.05 to about 3 phr, in order toactivate and to improve the properties of the vulcanizate. Combinationsof these accelerators might be expected to produce a synergistic effecton the final properties and are somewhat better than those produced byuse of either accelerator alone. In addition, delayed actionaccelerators may be used which are not affected by normal processingtemperatures but produce a satisfactory cure at ordinary vulcanizationtemperatures. Vulcanization retarders might also be used. Suitable typesof accelerators that may be used in the present invention are amines,disulfides, guanidines, thioureas, thiazoles, thiurams, sulfenamides,dithiocarbamates and xanthates. Preferably, the primary accelerator is asulfenamide. If a second accelerator is used, the secondary acceleratoris preferably a guanidine, dithiocarbamate or thiuram compound.

The mixing of the rubber composition can be accomplished by methodsknown to those having skill in the rubber mixing art. For example theingredients are typically mixed in at least two stages, namely at leastone non-productive stage followed by a productive mix stage. The finalcuratives including sulfur vulcanizing agents are typically mixed in thefinal stage which is conventionally called the “productive” mix stage inwhich the mixing typically occurs at a temperature, or ultimatetemperature, lower than the mix temperature(s) than the precedingnon-productive mix stage(s). The rubber, silica, siloxy compound ofFormula I and carbon black, if used, are mixed in one or morenon-productive mix stages. The terms “non-productive” and “productive”mix stages are well known to those having skill in the rubber mixingart. The sulfur vulcanizable rubber composition containing the siloxycompound of Formula I, vulcanizable rubber and generally at least partof the silica should, as well as the sulfur-containing organosiliconcompound, if used, be subjected to a thermomechanical mixing step. Thethermomechanical mixing step generally comprises a mechanical working ina mixer or extruder for a period of time suitable in order to produce arubber temperature between 140° C. and 190° C. The appropriate durationof the thermomechanical working varies as a function of the operatingconditions and the volume and nature of the components. For example, thethermomechanical working may be from 1 to 20 minutes.

Vulcanization of the rubber composition of the present invention isgenerally carried out at conventional temperatures ranging from about100° C. to 200° C. Preferably, the vulcanization is conducted attemperatures ranging from about 110° C. to 180° C. Any of the usualvulcanization processes may be used such as heating in a press or mold,heating with superheated steam or hot air or in a salt bath.

Upon vulcanization of the sulfur vulcanized composition, the rubbercomposition of this invention can be used for various purposes. Forexample, the sulfur vulcanized rubber composition may be in the form ofa tire, belt or hose. In case of a tire, it can be used for various tirecomponents. Such tires can be built, shaped, molded and cured by variousmethods which are known and will be readily apparent to those havingskill in such art. Preferably, the rubber composition is used in thetread of a tire. As can be appreciated, the tire may be a passengertire, aircraft tire, truck tire and the like. Preferably, the tire is apassenger tire. The tire may also be a radial or bias, with a radialtire being preferred.

While certain representative embodiments and details have been shown forthe purpose of illustrating the invention, it will be apparent to thoseskilled in this art that various changes and modifications may be madetherein without departing from the spirit or scope of the invention.

What is claimed is:
 1. A method of processing a rubber composition whichcomprises mixing (i) 100 parts by weight of at least one sulfurvulcanizable elastomer selected from conjugated diene homopolymers andcopolymers and from copolymers of at least one conjugated diene andaromatic vinyl compound; with (ii) 0.05 to 10 phr of a compound of theformula:

where R¹, R² and R³ are independently selected from alkoxy radicalshaving from 1 to 8 carbon atoms; R⁴ and R⁵ are independently selectedfrom the group consisting of alkylenes having 1 to 12 carbon atoms,arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbonatoms and n is an integer of from 1 to
 10. 2. The method of claim 1wherein the compound of Formula I is selected from the group of formulaeconsisting of:

wherein x and y are individually selected from a group of integers offrom 1 to 12 and R⁶ is a cycloaliphatic group having from 5 to 8 carbonatoms in the ring.
 3. The method of claim 1 wherein from 10 to 150 phrof filler is present during mixing.
 4. The method of claim 3 whereinsaid filler is silica.
 5. The method of claim 1 wherein said sulfurvulcanizable elastomer containing olefinic unsaturation is selected fromthe group consisting of natural rubber, neoprene, polyisoprene, butylrubber, halobutyl rubber, polybutadiene, styrene-butadiene copolymer,styrene/isoprene/butadiene rubber, methyl methacrylate-butadienecopolymer, isoprene-styrene copolymer, methyl methacrylate-isoprenecopolymer, acrylonitrile-isoprene copolymer, acrylonitrile-butadienecopolymer, EPDM, silicon-coupled star-branched polymers, tin-coupledstar-branched polymers, siloxy-terminated elastomers and mixturesthereof.
 6. The method of claim 1 wherein said rubber composition isthermomechanically mixed at a rubber temperature in a range of from 140°C. to 190° C. for a mixing time of from 1 to 20 minutes.
 7. The methodof claim 3 wherein said filler is selected from the group consisting ofcarbon black, aluminasilicates, clays, zeolites, modified starches andsilica/carbon composites.
 8. A sulfur vulcanizable rubber compositioncomprising an elastomer containing olefinic unsaturation and a compoundof the formula:

where R¹, R² and R³ are independently selected from alkoxy radicalshaving from 1 to 8 carbon atoms; R⁴ and R⁵ are independently selectedfrom the group consisting of alkylenes having 1 to 12 carbon atoms,arylenes having 6 carbon atoms and alkarylenes having 7 to 10 carbonatoms and n is an integer of from 1 to
 10. 9. The composition of claim 8wherein the compound of Formula I is selected from the group consistingof:

wherein x and y are individually selected from a group of integers offrom 1 to 12 and R⁶ is a cycloaliphatic group having from 5 to 8 carbonatoms in the ring.
 10. The composition of claim 8 wherein from 10 to 150phr of filler is present during mixing.
 11. The composition of claim 10wherein said filler is silica.
 12. The composition of claim 8 whereinsaid compound of Formula I is present in an amount ranging from 1 to 5phr.
 13. The composition of claim 8 wherein said elastomer containingolefinic unsaturation is selected from the group consisting of naturalrubber, neoprene, polyisoprene, butyl rubber, halobutyl rubber,polybutadiene, styrene-butadiene copolymer, styrene/isoprene/butadienerubber, methyl methacrylate-butadiene copolymer, isoprene-styrenecopolymer, methyl methacrylate-isoprene copolymer,acrylonitrile-isoprene copolymer, acrylonitrile-butadiene copolymer,EPDM, silicon-coupled star-branched polymers, tin-coupled star-branchedpolymers, siloxy-terminated elastomers and mixtures thereof.
 14. Thecomposition of claim 8 wherein said composition is thermomechanicallymixed at a rubber temperature in a range of from 140° C. to 190° C. fora total mixing time of from 1 to 20 minutes.
 15. The composition ofclaim 10 wherein said filler is selected from the group consisting ofcarbon black, aluminasilicates, clays, zeolites, modified starches andsilica/carbon composites.
 16. A sulfur vulcanized rubber compositionwhich is prepared by heating the composition of claim 7 to a temperatureranging from 100° C. to 200° C. in the presence of a sulfur vulcanizingagent.
 17. The sulfur vulcanized rubber composition of claim 16 in theform of a tire, belt or hose.
 18. A tire having a tread comprised of thecomposition of claim 16.